Aluminum(III) Chloride → HCID 19047070, compound

HRID 1780614Notes

Reaction equation

HRID 1780614 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Al+3].[Cl-].[Cl-].[Cl-].[CH3:11][C:12]1([CH3:25])[CH2:16][C:15]2[C:17]([CH3:24])=[C:18]([CH:22]=O)[CH:19]=[C:20]([CH3:21])[C:14]=2[O:13]1>C(OCC)C>[CH3:11][C:12]1([CH3:25])[CH2:16][C:15]2[C:17]([CH3:24])=[C:18]([CH3:22])[CH:19]=[C:20]([CH3:21])[C:14]=2[O:13]1

Participants

5

Reactant 3

HCID 6451240Aluminum(III) Chloride2×HCID 19047059HCID 19047059, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19047070HCID 19047070, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of 9.75 g of lithium aluminum hydride in 200 ml of absolute diethyl ether was added 34.27 g of AlCl3 and added dropwise a mixture of 42 g of the 2,3-dihydro-2,2,4,7-tetramethylbenzofuran-5-carboxaldehyde and 27.4 g of AlCl3 in 100 ml of absolute diethyl ether. After stirring for 30 minutes, the reaction mixture was quenched with 10 ml of ethyl acetate and added with 100 ml of water and 100 ml of 2N aqueous solution of hydrochloric acid. The organic extract was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford a crude product. Final purification was carried by vacuum distillation to afford 34.5 g of 2,3-dihydro-2,2,4,5,7-pentamethylbenzofuran as colorless oil.

Workup

  1. additionadded dropwise
  2. customthe reaction mixture was quenched with 10 ml of ethyl acetate
  3. additionadded with 100 ml of water and 100 ml of 2N aqueous solution of hydrochloric acid
  4. extractionThe organic extract
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto afford a crude product
  9. customFinal purification
  10. distillationwas carried by vacuum distillation

Sources & evidence

ORD record
ord-732d31f969a24baaafd92a31af1a9ef9
Source dataset
uspto-grants-1997_05
Patent number
US05631208

Reaction notes

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